(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid

• ChemBase ID: 45
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: OC(=O)CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
• InChI: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChIKey: JAZBEHYOTPTENJ-JLNKQSITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoic acid
• IUPAC Traditional name: eicosapentaenoic acid; icosapent
• Synonyms: (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid; (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid; EPA 45G; Icosapent; Incromega E 7010SR; Ropufa 70; Eicosapentaenoic Acid; cis-5,8,11,14,17-Eicosapentaenoic acid; Eicosapentaenoic acid; EPA; Icosapentaenoic acid; Timnodonic acid; Icosapent; 二十碳五烯酸; 顺式-5,8,11,14,17-二十碳五烯酸

Database IDs

• CAS Number: 10417-94-4
• MDL Number: MFCD00065716
• Beilstein Number: 1714433
• PubChem SID: 46506267; 24868422; 160963508; 24894450; 24894640
• PubChem CID: 446284

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.819772
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4632735
• LogD (pH = 7.4): 3.6901412
• Log P: 6.2252493
• Molar Refractivity: 101.0706 cm^3
• Polarizability: 36.914207 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 6.53
• LOG S: -6.02
• Solubility (Water): 2.89e-04 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Colorless Oil; liquid
• Melting Point: -54--53 °C(lit.)
• Flash Point: 199.4 °F; 93 °C
• Density: 0.943 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.4977(lit.)
• Hydrophobicity(logP): 6.1

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3265 8/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ALOX5(240)mouse ... ALOX5(11689), Pparg(19016)rat ... ALOX5(25290); mouse ... Pparg(19016)

Product Information

• Purity: ≥85%; ≥97.0% (GC); ≥98.5% (GC); ≥99%
• Grade: analytical standard; purum
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: CH3(CH2CH=CH)5(CH2)3CO2H

DETAILS

DrugBank - DB00159

• Drug Groups: approved; nutraceutical
• Description: Important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. [PubChem]
• Indication: EPA can be used for lowering elevated triglycerides in those who are hyperglyceridemic. In addition, EPA may play a therapeutic role in patients with cystic fibrosis by reducing disease severity and may play a similar role in type 2 diabetics in slowing the progression of diabetic nephropathy.
• Pharmacology: Eicosanoids are chemical messengers derived from 20-carbon polyunsaturated fatty acids that play critical roles in immune and inflammatory responses. Both 20-carbon omega-6 fatty acids (arachidonic acid) and 20-carbon omega-3 fatty acids (EPA) can be found in cell membranes. During an inflammatory response, arachidonic acid and EPA are metabolized by enzymes known as cyclooxygenases and lipoxygenases to form eicosanoids. Increasing omega-3 fatty acid intake increases the EPA content of cell membranes and decreases the arachidonic acid content, resulting in higher proportions of eicosanoids derived from EPA. Physiologic responses to arachidonic acid-derived eicosanoids differ from responses to EPA-derived eicosanoids. In general, eicosanoids derived from EPA are less potent inducers of inflammation, blood vessel constriction, and clotting than eicosanoids derived from arachidonic acid.
• Affected Organisms: Humans and other mammals
• External Links: PDRhealth

Sigma Aldrich - E7006

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。
包装
5, 10, 25, 50 mg in ampule
Sealed ampule.

Sigma Aldrich - E2011

Biochem/physiol Actions
5-脂氧合酶抑制剂；减少凝血噁烷 A2 生成。

Sigma Aldrich - 44864

Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

Sigma Aldrich - 44865

Biochem/physiol Actions
5-Lipoxygenase inhibitor; reduces thromboxane A2 production.

Toronto Research Chemicals - E477800

Important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thrombox

REFERENCES

• Bergstrom, S., et al.: J. Biol. Chem., 239, PC 4006 (1964)
• Srivastava, K.C., et al.: Biochem. Exp. Biol., 16, 317 (1964)
• Kremer, J.M., et al.: Ann. Intern. Med., 106, 497 (1964)
• DiGiacomo, R.A., et al.: Am. J. Med., 86, 158 (1964)